Dorset Boltholes with Enclosed Gardens

Dorset Boltholes with Enclosed Gardens

In a self-catering cottage with an enclosed garden you and your family can enjoy some added privacy and security. Help contain lively legs and take a look at our luxury portfolio in Dorset. At Classic Cottages, we want your whole experience to be the best it can be and handpick all of our cottages onto our books. Find your cottage today for dreams tomorrow. Read more

Whether you are looking for family-friendly accommodation or a dog-friendly cottage with an enclosed garden, we have a selection of properties available in Dorset for you to choose from. To give you some added reassurance, let your kids play and your dog sniff around in a garden offering more security. You'll be able to relax knowing your loved ones are nearby.

Cottages with Enclosed Gardens in Dorset 

Across Dorset we have a range of beautiful self-catering cottages of all shapes and sizes. Priding ourselves on marketing only the finest self-catering accommodation around, we want your holiday in Dorset to be the best it can be. Browse our selection of 15 available retreats with enclosed gardens and find your perfect one. The holiday of a lifetime is but moments away. 

15 retreats with enclosed gardens in Dorset

2 Penny’s Cottages is a 3 bedroom house in the historic village of Corfe Castle, Dorset.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £723

2 Penny’s Cottages

2531

3 bedroom house in the historic village of Corfe Castle, Dorset.


Set in the historic village of Corfe Castle, 2 Penny's Cottages is a semi-detached family house that welcomes all its visitors, it is a real home-from-home. The property has been b...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £723

Sunnyholme is a 4 bedroom house near the beach in Studland, Dorset.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £805

Sunnyholme

1460

4 bedroom house near the beach in Studland, Dorset.


The Isle of Purbeck is a stunning National Landscape between Poole and Swanage boasting one of the most spectacular coastlines in Dorset. Sunnyholme is an extremely spacious det...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £805

Sandy Days is a 3 bedroom, dog friendly cottage near the beach in Christchurch.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £898

Sandy Days

3215

3 bedroom, dog friendly cottage near the beach in Christchurch.


Avon beach, Christchurch Harbour, the New Forest National Park and the Jurassic Coast are all nearby to this holiday bolthole. The cool shades of blue and the plantation shutters e...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £898

The Old Manor House is a 5 bedroom, dog friendly cottage close to the beach near Lyme Regis.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1853

The Old Manor House

4124

5 bedroom, dog friendly cottage close to the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1853

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West Hembury Farm

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1089